4-acetyl-1,5-dimethylimidazole-2(3H)-thione | 1310826-08-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetyl-1,5-dimethylimidazole-2(3H)-thione
• 英文别名: 1-(3,4-dimethyl-2-sulfanylidene-1H-imidazol-5-yl)ethanone
• CAS: 1310826-08-4
• 化学式: C₇H₁₀N₂OS
• 分子量: 170.235
• InChiKey: UVYPFUCJDZLSGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3,4-戊三酮肟 (6ci,7ci,8ci,9ci) 以 乙醚 、 氯仿 为溶剂， 生成 4-acetyl-1,5-dimethylimidazole-2(3H)-thione
  参考文献：
  名称：

  Synthesis of New Imidazole 3-Oxides; Unexpected Deoxygenation of Some Derivatives in the Reaction with 2,2,4,4-Tetramethylcyclobutane-1,3-dithione

  摘要：

  Whereas the reaction of a series of 1,4,5-trisubstituted imidazole 3-oxides with 2,2,4,4-tetramethylcyclobutane-1,3-dithione gave the corresponding imidazole-2-thiones by a sulfur-transfer reaction via [2+3] cycloaddition, an unexpected deoxygenation occurred in the case of 4-acetyl-1-(adamantan-1-yl)-5-methylimidazole 3-oxide. It was shown that the presence of an electron-withdrawing substituent at C(4) and the bulky 1-adamantyl group at N(1) are necessary to enable this reaction course. A reaction mechanism via a zwitterion, followed by a 1,3-cyclization and elimination of an oxathiirane, is proposed.

  DOI：

  10.3987/com-10-12130

文献信息

• Synthesis of New Imidazole 3-Oxides; Unexpected Deoxygenation of Some Derivatives in the Reaction with 2,2,4,4-Tetramethylcyclobutane-1,3-dithione
  作者：Grzegorz Mlostoń、Heinz Heimgartner、Marcin Jasinski、Dorota Rygielska

  DOI：10.3987/com-10-12130

  日期：——

  Whereas the reaction of a series of 1,4,5-trisubstituted imidazole 3-oxides with 2,2,4,4-tetramethylcyclobutane-1,3-dithione gave the corresponding imidazole-2-thiones by a sulfur-transfer reaction via [2+3] cycloaddition, an unexpected deoxygenation occurred in the case of 4-acetyl-1-(adamantan-1-yl)-5-methylimidazole 3-oxide. It was shown that the presence of an electron-withdrawing substituent at C(4) and the bulky 1-adamantyl group at N(1) are necessary to enable this reaction course. A reaction mechanism via a zwitterion, followed by a 1,3-cyclization and elimination of an oxathiirane, is proposed.